


Please

by YlvaUllsdotter



Series: SPN Kink Bingo 2019 [12]
Category: Supernatural
Genre: Begging, Blood, Burning, Dark fic, F/M, Flogging, Pegging, Rape, SPN Dean Bingo, Sort Of, Strap-On, Sub!Dean, Supernatural Kink Bingo 2019, Torture, non-con
Language: English
Status: Completed
Published: 2019-06-10
Updated: 2019-06-10
Packaged: 2020-04-24 02:50:34
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 1
Words: 3,808
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19164301
Author URL: https://archiveofourown.org/users/YlvaUllsdotter/pseuds/YlvaUllsdotter
Summary: She is a demon, tasked with torturing the location of the Winchester’s half of the demon tablet out of Dean. It will be a challenge, but she looks forward to it.





	Please

**Author's Note:**

> Written for both @spnkinkbingo and @spndeanbingo  
> Square filled (Kink Bingo): Begging  
> Square filled (Dean Bingo): Torture
> 
> This is a dark!fic. Please mind the tags.

****Dean drifted into consciousness like a diver rising through molasses. The first thing he became aware of was the steady _drip drip drip_ coming from somewhere above him. Slowly, his senses took stock of his surroundings. 

He was lying on a cold hard surface, probably smoothed concrete. His body hurt, but he seemed to be all in one piece and no broken bones. He had a bitch of a headache, but there was nothing he could do about that now, so he ignored it. Aside from the dripping, it was silent, no sounds of traffic or nature. The air was cool, but not cold. Also, he was naked.

Without opening his eyes, or moving, Dean tried to piece together his memories to figure out what had happened and where he was. 

He had been on a simple salt and burn, a milk run. Sam needed his rest, the Trials had really messed that kid up, and this one seemed like a lay-up, so he had gone alone. He had pulled up to the cemetery-- no he had already been grabbing the sawed-off and a shovel out of the trunk. No matter how hard he tried, Dean could not remember anything after that, it was just black.

With the headache that was pounding away at the back of his head, he figured someone, or something, must have gotten the drop on him and knocked him out. What he could not figure out was why he was naked in what he guessed was a cell. 

Resigned to the fact that there was nothing he could do to change his situation right at that moment, Dean stirred, slowly stretching stiff muscles and taking stock of his physical state. When he had determined that he was mostly fine, aside from a few bruises and the lump on the back of his head, he pulled himself up to a sitting position. Under the cover of further stretching, he took stock of the room he was in.

It was basically a concrete box with no windows and one door, which was made of metal, probably steel, and had a small hatch like a prison cell door. A single lightbulb encased in wire mesh sat high above the door. There was a bucket in one corner. In the center of the ceiling was a small semi-sphere of dark glass or plastic, something he had seen many times before and had in fact trained himself to notice wherever he went. A camera. 

Dean stared at the camera, willing the person on the other end to reveal themselves.

 

* * *

She sat in the uncomfortable desk chair, watching the monitor that showed the unconscious Dean Winchester. She could tell the exact moment when he went from actually unconscious, to just faking it, and waited patiently. Time had little meaning to someone like her and she had long ago learned that patience usually came with greater rewards.

The reward this time was getting her hands on Dean Winchester. Crowley thought he had chosen her for his own reasons, but she had made sure to be in the right place at the right time to be chosen. She would get the information the King wanted, but she would make sure to get it her own way, and she would enjoy every moment with the hunter.

Drawing the knife she carried strapped to her thigh, she idly tapped the razor-sharp tip against the scarred surface of the desk while she watched Dean move about. She appreciated his economy of movement, even in captivity. When he turned his eyes on the camera, she bared her teeth in a smile that would have made a regular human run screaming.

The chair wheels, stuck of course, scraped across the wooden floor when she stood up. The knife slid back into its sheath in the same smooth movement. The King did not have her patience, so she would get started, even though she would have preferred to let the hunter stew for a while in uncertainty.

* * *

Dean turned toward the door at the muffled sound of steps on the other side. It stopped and was immediately followed by the scraping of a bolt, and the slight squeak of a key being turned. In the back of his mind, he took pride in the fact that whoever, or whatever, had him prisoner considered him dangerous enough to lock him up that securely.

The door swung open smoothly enough, given the creak of the hinges, and Dean took in the figure standing in the opening. Heavy boots, probably steel-toed. Dark jeans that looked like they had been painted onto the shapely legs. A wide leather belt that had several items attached to it; Dean only recognized the cuffs, the rest was a mystery to him. A black leather jacket with enough straps and zippers to satisfy Edward Scissorhands, covering a simple black t-shirt, or possibly tank top. 

Dean squinted, but the light from outside the door was right behind the person’s head, leaving their face in shadow. From the legs, and the breasts, he could tell she was female but not much more. 

“Dean Winchester,” a surprisingly pleasant voice said.

“Found me,” Dean quipped, falling back into smartass mode automatically. He did not think this lady was there to rescue him for some reason.

“Always with the smart mouth. That’s ok, talk all you want. In fact, I want you to talk,” she retorted.

“Oh yeah? Whaddya wanna talk about? Weather? Sports?” Dean shot back, still on the floor, but gathering himself to spring when she got closer.

She took a step into the room, giving him a better look at her face. She was not bad looking, although the black eyes kind of spoiled it for him. He waited. Just one more step.

The smile on her face, along with the black eyes, was unsettling. Dean almost felt as if she had read his mind when she did take that step closer. Pushing the feeling aside, he sprang up, intending to headbutt her. He figured he might even knock her out with the force of his whole body behind the impact.

What he had not figured on was being caught in mid-stride by the invisible force of her demon power. He hung in mid-air, unable to move anything but his eyes. They flicked up to her face, where that unsettling smile still sat unchanged.

“It was a nice try, Dean, and totally in character for you. Never give up, right? Fight until your last breath? All that? It’s honestly adorable.” 

She moved closer as she spoke until she was standing only inches away and his eyes ached from the strain of keeping her face in sight. Standing so close, she cupped his chin in her hand and raised his head, relieving some of the strain. 

“I’m gonna have so much fun with you,” she told him levelly, before letting go and turning to leave.

For a moment, Dean panicked that he was going to be left like that, but when she passed through the open door, her power released him and he slumped to the floor. Immediately, he sprang up and threw himself at the doorway, only to slam into a wall of muscle. 

Staggering back, Dean shook his head to clear his vision. The doorway was filled by something the size of a grizzly bear and only slightly less hairy. The eyes flashed to black and the demon took a step into the cell, Dean automatically stepping back to keep his distance.

Another thug stepped in after the first. The two of them advanced steadily on Dean until they had backed him into a corner. Each of them wrapped a ham-sized fist around one of Dean’s arms and dragged him with them out the door, following the receding form of the female demon.

He was dragged along too quickly for him to even consider trying to get to his feet. Instead, he let himself go limp, adding to the weight the two black-eyed thugs had to carry. It was a petty thing, but it was the only way he could resist, and he was going to resist to his last breath.

In the low light of the hallway, Dean could make out regularly spaced doors, most standing open, a couple looking like they had been ripped off their hinges. Rounding a corner, he noticed light streaming from one of them and assumed that was their destination. 

Every instinct told him to prepare to fight, but he pushed it down. There was no chance of fighting free at this point, not with the two demon thugs right there, not to mention the physical state he was in. He would just have to bide his time and wait for an opportunity.

While Dean struggled with his instincts, they had reached the lit doorway. The goons dragged him inside and over to one side of the room. While they manhandled him as if he was a ragdoll, Dean did his best to take stock of the room.

Superficially it looked a lot like his cell; a concrete box with no windows and only the one door. It had the camera and the lightbulb over the door. It also held a number of metal tray tables covered in various items. Dean could see at least a dozen different blades and a great many things he had never seen before. It was not difficult to figure out what it was all for though. 

The sound and feel of metal closing around his wrists caught his attention, and he watched as his arms were hoisted above his head by a chain. The demon operating the chain grinned as he pulled it tighter, forcing Dean up on his toes, before securing the chain to a ring on the wall. 

Dean felt the panic rise like bile in his throat. The manacles, the chains, the room, it all reminded him a little too much of Hell. It made no difference that this time it was all too substantial. He tried to take the weight off his wrists by standing straighter, but the steel still bit into his flesh in a way that made him want to scream.

Struggling with the panic, he heard the tread of her heavy boots before she entered the room.

“Get out,” she hissed curtly at the two minor demons, who quickly scurried out of her way.

She slammed the door shut behind them, then turned to look at Dean. Crossing her arms, she stood there in silence and just watched him. Dean got the feeling she was waiting for him to make the first move, he just had no idea what she expected him to do, trussed up as he was. 

His legs were already starting to tremble from the position he was forced to maintain, up on his toes. Finally, the silence grated on him so much he could no longer keep his mouth shut.

“Nice place you’ve got here. Very torture dungeon chic,” he quipped, although without the usual level of snarkiness behind it.

As if his comment was what she had been waiting for, she uncrossed her arms and moved towards him. Still saying nothing, she patted his face in a mockery of reassurance, hard enough to leave a warm feeling behind. She was smiling again, that unsettling smile that was more of a snarl, and Dean wanted to flinch away from her.

Her fingers trailed from his face, down his neck, and came to rest on his collarbone briefly. She traced the outline of the slender bone with her thumb and index finger on either side of it. Dean was just starting to wonder what she was up to when he felt the pressure of her touch increase, followed by a brittle snap and a white-hot pain lancing through him from the point of the break. 

He screamed. There was nothing else to do, the pain was too intense to work through any other way. The way he was strung up, arms above his head, the pain just went on and on. Finally, his body adjusted enough that he was able to breathe. He tried to look down to see how much damage she had done, but the angle was wrong. Instead, he looked into her black eyes and snarled.

Her smile widened at his reaction, and she trailed her fingers down from the broken collarbone, tracing the muscles covering his ribs. He felt every inch of her touch, her fingers leaving behind blistering welts as if drawn with fire, all the way down to his hip.

Dean clenched his teeth to stop the sound escaping him, but the whimper filtered out anyway, against his will. She drew it from him like he was an instrument and she was a virtuoso. 

Through his own whimpers of pain, Dean heard her speak, at last, her tone conversational.

“I trained under Alastair, Dean. Did you know that? You can fight me all you want, you know you’ll break in the end. Just like you did in Hell.”

Her fingers traced a burning trail across his pelvis, then started on an upward trail along his other side. Dean hated himself for not doing a better job of resisting her. She had only just started and already he was a whimpering mess. 

“Of course, reality up here is more limited than down in the Pit. I have to take care not to kill you too quickly. You’ll be happy to know that I’ve had plenty of practice. It’s likely I’m better than Alastair ever was.”

When she reached his other collarbone, Dean tried to flinch away in anticipation of what she might do. It only made her grin widen when she moved away from him, giving him an unexpected chance to breathe and adjust to the pain of the burns.

His eyes followed her as she moved to the line of tray tables along the wall, running her hands over the various items laid out there. The pain was making it difficult to think straight or to focus on what she was doing, so he missed seeing what she had picked up until she turned around again.

In her hand was what Dean could only describe as a fighting baton. It looked a lot like the nightsticks used by police in some larger cities; a smooth rod just over a foot in length, with a slimmer handle sticking out at a right angle near the butt end. 

Rather than watch her hands, Dean focused on the inky black of her eyes when she approached again. Without warning, she jabbed the rod into his solar plexus, driving the air from his lungs.

Dean’s body tried to curl in on itself and he struggled to pull breath into his shocked lungs. He started to panic when nothing happened, his vision narrowing as he approached unconsciousness. The tiny breath he finally was able to pull in was just enough to keep him conscious. He was not entirely sure that was a good thing. Maybe if he had passed out, it would have been a break from the pain. 

“Don’t worry,” she said in what passed for a reassuring tone from a demon, “I won’t let you pass out. Not yet.”

Panting, his lungs still recovering, Dean questioned her motives.

“Why...are you...doing this?”

“Yes, good question. I suppose I should clarify while you can still understand me,” she mused, tapping the baton against her palm. “Your prophet has hidden your half of the demon tablet. You’re going to tell me where it is.”

“Screw...you,” Dean managed in between labored breaths.

“Eloquent as always. You’ll tell me before you die,” she replied.

Immediately on the heels of her statement, she slammed the length of the rod against his side, the thud of it impacting Dean’s flesh followed by another brittle snap and a lightning bolt of pain lancing through him.

“That’s one. Twenty-three more to go,” she informed him while he writhed with pain.

Dean’s pain-fogged mind raced. He had no idea where Kevin had hidden their half of the demon tablet. The kid was unhinged at best. Would this demon bitch believe him if he told the truth? Would it even matter? He suspected she would keep going either way, so what was there to gain from telling her? On the other hand, if he resisted her, he might buy enough time for Sam to find him. Provided his little brother’s head cleared enough to actually realize Dean was in trouble. How long might that take? A day? Two? Three? How long could he hold out? 

“What...makes you think...I know where...it is?” Dean managed between breaths.

Just about to break another rib, she paused, the baton lowering slightly.

“Because Crowley said so,” she told him evenly.

“Oh right...because that...limey bastard always...knows...what he’s talking...about,” Dean panted, each word causing pain to wrack his body.

She tilted her head and studied him, eyes narrowed. After an endless moment, she lowered the baton and stuck it behind her belt. 

“Still,” she told him, gripping his face in her hand, “I’m going to keep torturing you, just in case.”

He watched her until she disappeared from his line of sight, his body tensed, fighting the pain she had already inflicted. He felt his muscles constrict further in anticipation of what she might do.

He flinched when he felt something touch his face. The next instant, he felt it cover his eyes. A blindfold. The panic rose inside him again. Without being able to see his surroundings, each rattle of the chains brought up memories from Hell and made him want to scream.

“no no no no,” he caught himself mumbling and clenched his jaw shut to stop himself. He would not give her the satisfaction of begging.

Without warning, he felt burning lines of pain flash down his back and his scream echoed off the walls of the small room. When he ran out of breath, he heard her laugh behind him. 

Before he had time to recover and catch his breath, the all-too-familiar feeling of a flogger burned across his back. Each strand felt like it sliced through his skin, but with his teeth so tightly clenched, all that came out was a muffled grunt.

The strokes fell without mercy, one after the other, and soon he felt the warm trickle of blood making its way down his back and ass, dripping down his legs. He broke a little then, letting himself ride the waves of pain, and stopped holding the memories back.

She could tell when he gave in to the pain by the volume of his screams. She did not think he was even aware of the sounds he was making. In the darkness of his own mind, she had no doubt he was back in Hell, being tortured by hordes of demons, ripping and tearing at his flesh. 

Overcome with the images, and the scent of his blood and fear, she flicked her tongue out to wet her lips. She dragged her fingers through the mess of flesh and blood that was his back, the trails almost sizzling from the heat, then brought the fingers to her lips to taste him.

She knew she had to keep him alive until she got the information out of him, but when she tasted his blood, so full of fear and hatred, she almost forgot her orders. Eyes closed, she savored the taste, a shiver of desire running through her.

Drunk on his scent, her fingers fumbled with her clothes, and then the straps, finally getting the harness situated the way she wanted. Her hands burned when she grabbed his hips, leaving angry marks on his skin. She growled when she sank the fake cock into his ass, to the sound of his pained whine, the blood that had run down the crack of his ass the only lube she needed. The base of the silicone cock pressed against her clit and she set a hard pace from the start. 

Dean was so deep in his memories that he barely felt the new pain. It was only a drop in a sea of agony. Floating in that sea, Dean was drowning in sensations. There was too much and he had no time to process. 

The hand on his cock seemed to stroke in time with the waves of pain. Shame and embarrassment mixed with despair when he felt the pleasure wash through him. It was almost more painful than the actual torture.

“No, please...stop...I don’t...please…,” the words fell from Dean’s lips of their own accord.

She felt another shiver trace her spine hearing them. Making her victims beg had always been a favorite for her, but she had not expected to hear it from Dean Winchester. The sound of it made her increase the pace of her thrusts, her hand on his cock matching the speed.

“Come for me, Dean. Be a good boy for me. You wanna be good for me, don’t you? Come on, I want it,” she could not resist urging him on, her voice a hoarse whisper right by his ear.

Even now, he shook his head in denial, trying to hold back, trying to resist her. It only pushed her closer to the edge. She bit down on his shoulder, tasting his blood on her tongue. It was so delicious, she could not get enough. His defiance, even now, was the best aphrodisiac she had ever had and she was quickly approaching her peak.

Wanting to make him come first, she withdrew her fake cock from his ass, quickly undoing the straps and letting the whole contraption fall to the floor. Coming around to face him, she draped one leg over his hip, using her free hand to guide his cock into her dripping pussy and driving it home in a single thrust.

Her hands burned the skin of his ass when she pulled him closer and he ended up inadvertently thrusting into her to get away from the new pain. With one hand on his ass, and the other gripping his shoulder, she fucked him hard.

Dean shook his head, desperately trying to resist her, even now, and when he tensed and shot his load inside her, filling her up, tears trickled from underneath the blindfold. His grunts sounded suspiciously like sobs, and the sound pushed her over the edge into her own release.

Sated for the moment, she pushed away from him, the feeling of his spend dripping down her thighs a badge of triumph. She patted his cheek, almost fondly.

“Such a good boy, Dean. Now, let’s get back to the matter at hand,” she purred at him, before picking the flogger back up.


End file.
